$94 Find Cheap Flights from Chicago O'Hare Airport to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Caribbean Islands departing on 3/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from O'Hare Intl to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$291
Santo Domingo
Santo Domingo1 stop$301
Montego Bay
Montego Baynonstop$298
Oranjestad
Oranjestad1 stop$453
Nassau
Nassau1 stop$469
Kingston
Kingston1 stop$445
Simpson Bay
Simpson Bay1 stop$330
Providenciales
Providenciales1 stop$372
Port of Spain
Port of Spain1 stop$318
Bridgetown
Bridgetown1 stop$418
George Town
George Town1 stop$450
Willemstad
Willemstad1 stop$461
Castries
Castries2 stops$991
Puerto Plata
Puerto Plata1 stop$449
St. John's
St. John's1 stop$492
Aguadilla
Aguadilla1 stop$271
Punta Cana
Punta Cananonstop$291
Santo Domingo
Santo Domingo1 stop$301
Montego Bay
Montego Baynonstop$298
Oranjestad
Oranjestad1 stop$453
Nassau
Nassau1 stop$469
Kingston
Kingston1 stop$445
Simpson Bay
Simpson Bay1 stop$330
Providenciales
Providenciales1 stop$372
Port of Spain
Port of Spain1 stop$318
Bridgetown
Bridgetown1 stop$418
George Town
George Town1 stop$450
Willemstad
Willemstad1 stop$461
Castries
Castries2 stops$991
Puerto Plata
Puerto Plata1 stop$449
St. John's
St. John's1 stop$492
Aguadilla
Aguadilla1 stop$271

Book Cheap O'Hare Intl to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Caribbean Islands

Sun, May 17 - Fri, May 29
Frontier Logo
8:24 pm - 11:02 pm
ORD
-
SJU
25h 38m
1 stop
Frontier Logo
8:10 pm - 12:25 am
SJU
-
ORD
5h 15mnonstop
$192Frontier
Mon, May 4 - Fri, May 8
Spirit Airlines Logo
7:50 am - 2:06 am
ORD
-
SJU
17h 16m
1 stop
Spirit Airlines Logo
3:21 am - 2:05 pm
SJU
-
ORD
11h 44m
1 stop
$193Spirit Airlines
Mon, Apr 13 - Sat, Apr 18
Arajet Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
$291Arajet
Mon, Apr 20 - Sat, Apr 25
Arajet Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
$292Arajet
Sun, Apr 19 - Thu, Apr 23
United Airlines Logo
8:40 am - 12:50 pm
ORD
-
MBJ
4h 10mnonstop
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
$298United Airlines
Sun, Jun 7 - Thu, Jun 11
American Airlines Logo
5:00 am - 1:55 pm
ORD
-
MBJ
8h 55m
1 stop
American Airlines Logo
2:30 pm - 7:16 pm
MBJ
-
ORD
4h 46mnonstop
$302American Airlines
Wed, May 27 - Mon, Jun 1
American Airlines Logo
9:20 am - 1:30 pm
ORD
-
MBJ
4h 10mnonstop
American Airlines Logo
2:30 pm - 7:16 pm
MBJ
-
ORD
4h 46mnonstop
$303American Airlines
Sun, Apr 19 - Thu, Apr 23
United Airlines Logo
8:40 am - 12:50 pm
ORD
-
MBJ
4h 10mnonstop
United Airlines Logo
4:12 pm - 11:43 pm
MBJ
-
ORD
7h 31m
1 stop
$308United Airlines
Wed, Jun 3 - Tue, Jun 9
JetBlue Logo
6:00 am - 3:05 pm
ORD
-
AUA
8h 05m
1 stop
JetBlue Logo
4:35 pm - 7:35 pm
AUA
-
ORD
28h 00m
2 stops
$456JetBlue
Tue, Apr 7 - Mon, Apr 13
JetBlue Logo
7:45 am - 4:53 pm
ORD
-
GCM
9h 08m
1 stop
JetBlue Logo
4:59 pm - 7:41 am
GCM
-
ORD
14h 42m
1 stop
$460JetBlue
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Caribbean Islands flights

Get data-powered insights and trends into flights from O'Hare Intl to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Chicago O'Hare Intl Airport found in the last 72 hours was to San Juan, at $177 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $177.

What is the cheapest time of day to fly to Caribbean Islands?

The average price for all round-trip flights from Chicago O'Hare Intl Airport to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $352 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $481.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $431, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Caribbean Islands is September, when tickets cost $315 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $523 and $443 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Caribbean Islands?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago O'Hare Airport to Caribbean Islands, look for departures on Mondays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean Islands, Friday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago O'Hare Airport to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago O'Hare Airport to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago O'Hare Airport to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Chicago O'Hare Airport to the following destinations at these prices or less: San Juan $142 one-way - $282 round-trip

Reviews of the top 5 airlines serving from O'Hare Intl to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9413 reviews
7.3Comfort
6.6Food
7.7Boarding
7.1Entertainment
8.1Crew
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

My flight was delayed by over an hour and the turbulance was horrible.

Everything is an additional fee. No one said anything when I checking in and got my boarding pass about my small carry on suitcase. Charged me $100 at the gate for that little bag that I still had to take with me. Delays for both flights for no reason and then when I asked everyone said something different. Never flying spirit again. If it was just one thing maybe. This was a show from the minute I got to the airport.

I had a great experience from booking to boarding to landing. This was the best experience from all the flights I’ve had with Spirit so far! The price and times were affordable and perfect. I will fly with them again soon!

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

First off, I had a conversation with a flight attendant that was working this flight. I overheard her telling another flight attendant while we were in line for Chic-Fil-A that the flight was not going to land until 12:47 pm. I found this odd since the flight was to take off at 1:03. I commented to the flight attendant that was going to mess up the on-time take-off She said. if you fly alot you will notice that it's a good thing if the flight even arrives at all. I said that was a low bar. I think that flight attendants represent their airlines whether on board or in the airport ordering food. I was surprised to hear such negativity. However, I have noticed that Spirit flight attendants are usually in a sour mood.. Eventually the flight arrived and I boarded and the flight took off an hour late. There was no direction about the on-board wi-fi. Nor was there any info in the seat back pocket. I don't know if there was wi-fi or not, There were no complimentary snacks or drinks for my row 36 as there was turbulence and the captain asked the flight attendants to stop serving just as they were close to my row. When the turbulence stopped, they did have time to serve us but they did not. Upon arriving, the flight attendant asked anyone not having to catch a flight to Ft. Laudersle which was a tight connection to sit down and let those people pass. I complied but I could not help thinking that if Spirit would have took off on time that they would not have to inconvenience their passengers. All in all, I think Spirit is a mediocre airline at best. There are so many things they could do to improve. Yet, since I only fly Spirit infrequently preferring Southwest and Delta, I like to see if they are improving and sadly no, they are not. One good thing - nice modern seats and interiors.

I have to wait for the flight for 3 hours. The gate was switching for 5 times. Made feel frustrated. Delays took all my sleep. I went to work without any sleep.

Staff was good! Didn't like how slow the luggage return was

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports